Proposal Presentation: Proposal Before or During?

I think you just go down the list in priority of the method you want to use. First, request an in-person meeting, explaining why you feel that's best for them. If they push back, propose your second best option which is probably a web meeting to walk through it then send the proposal at the end. And if you get pushed hard on both of those, send and cross your fingers. Just be firm, know where the line is to push towards, justify it to them and do your best. I've been involved in situations where the prospect has very strict guidelines or requirements, must treat all the bidders exactly the same and for that reason can only accept emailed proposals with no opportunity to explain or talk through unless they contact the bidder.

Hard to imagine someone buying $100K++ software and not wanting to meet face to face for almost everything (How else are they going to take advantage of all the steaks and strippers you'll need to buy them?). They may want to see a copy of the proposal before the meeting but not in place of it. You may have a tough time getting all the decision makers in the room for the proposal.

I'm guessing if they fight it too much, consider it a red flag that the project is not a high-priority or they've set their minds on another product and are stringing you along.

I think most people will want to see a proposal before hand, even if a meeting is scheduled. They would like to prepare for the meeting as much as anyone.

One approach I'm currently using with a proposal I have in progress: We already scheduled a meeting to discuss the proposal even before I've put it together, and I will be emailing them that proposal a few days before the meeting.

That being said: I hate software development proposals. For the record. ;-)

The proposal should be a summary of earlier discussions. There should be no surprises in the proposal, including the price. (It's OK to have a detailed price in the proposal, as long as it was within the ballpark already discussed.) I send my proposals online. Prior to that, I would send by email. There was rarely an in-person meeting to review the proposal. There were usually in-person meetings to discuss the problem and devise the solution, however.